The New Terrain

I might have been ahead of my time.

Indulge me here, I’m about to wax nostalgic about some glory days. I promise to connect the dots right back to where you might be now.

Shortly after that summer I spent searching Prospect Park for my soul, I was invited to manage a sketch comedy group.

I knew them well - we were friends and I had helped them produce their live theater shows. YouTube launched in 2005, and by 2006 we started translating their stage work into low budget sketch videos, shooting mostly out in Brooklyn, including a few in my own apartment. Funny writing paired with great acting that generated clean-cut, character-driven comedy. YouTube was the place to find the larger audience they deserved.

By 2010, one of their videos exploded. ‘Going viral’ really meant something back then, kids. A few million views, subscribers surging into the tens of thousands. This was Lonely Island, Double-Rainbow Guy level. Mindblowing. More viral videos would follow, the channel started making a little revenue, and we launched a college tour.

Then, the Brands started calling.

Suddenly I was chatting up execs at PR firms and ad agencies. The same world I'd joked about retiring from had pulled me back in, but this time the experience had a whole different energy.

We were producing branded content before anyone had a name for it. Long before the creator economy was even a concept, I was defending the group's well-defined brand of comedy against corporate giants' expectations of them.

For my personal trajectory, this moment felt like validation: the leap I'd taken was actually leading to tangible new work. I could pour everything I'd learned in my career into collaborations with close friends who made me laugh, made me proud, and were genuinely breaking new ground.

I embedded myself in the office of a veteran comedy manager to learn more, expanded the group's touring and merch business, and explored whether I’d want to build a bigger roster of comics. Later, I’d find myself sitting in Lorne Michaels’ famous office at 30 Rock, considering a deal to join his network of YT channels, at the start of the ‘MCN’ days. We’d ultimately seek out sitcom glory in LA, but that’s a tale for another time. Back to the brands.

Almost every one of them made the same mistake.

They’d see a YouTube channel with a loyal audience in a specific demographic, and treat it like another billboard. The comedy group’s brand - their voice, their style, their hard-earned relationship with their audience, was merely a delivery mechanism to an advertiser, or just a set of characters to fit into a brand’s existing campaign.

I’d have to jump on many calls to convince the company or their agency that we were a self-sustaining creative force, one that had a dialed-in relationship with their audience and knew exactly how to write for them. The priority needed to be material that was authentic to our brand first, in order to create more fruitful results for everyone when we integrated their brand message.

Occasionally, a brand or agency would show up curious and ready to collab. They'd ask the group what they thought could actually work. They'd let the product get woven into the writing authentically, on the group's terms, in the group's voice.

Those partnerships were special. The production experience was joyful. The audience was receptive. The work was good. Everyone won.

I grew frustrated with many of the experiences but still worked these deals, on the chance they’d be collaborative, and that they’d help elevate our distribution. I was convinced that the entire industry would ultimately head our way. Strangely, it would take another fifteen years for them to fully grasp the concept.

From SXSW to Cannes this year, the creator economy has been roaring. We’re hearing frequent declarations that brand partnerships built on creative control and authentic collaboration outperform everything else. Creators who have built genuine, direct relationships with their audiences are being celebrated as the most valuable marketing partners in the ecosystem. The emphasis continues to shift from audience size and views to the quality and engagement of a creator’s community.

Ok, as promised, now back to you.

So how does any of this relate to a creative type looking for direction, or a professional stuck between their past successes and current confusion? As I’ve written, I was only able to discover my own new trajectory by pausing and looking inward, before heading back out there. And when I did emerge, I discovered a whole new set of possibilities that weren’t available to me previously.

My overall point today is that despite all the reports that the sky is falling, that your industry is ‘cooked’, that the work is evaporating - well, the work hasn’t disappeared - it’s simply relocating. Let’s survey the landscape.

Brand studios and in-house content silos are reportedly committing close to two million dollars on average toward sustained creator partnerships, ones that require real production expertise to deliver. A producer who has spent decades managing high-end shoots is needed back on set right now. The experienced creative team who is adept at leading production vendors, serving internal brand clients, and engaging external celebrities, is exactly whom these projects need right now.

Meanwhile, larger creators are operating like small media companies these days. Aside from producing shows, they’re launching products, running podcasts, and building communities with genuine commercial infrastructure built in. They are scaling fast and bringing people on with the expertise needed to run productions at a professional level. These creators need your help too.

Back when we started out, YouTube was still a curiosity. There were roughly 200 million monthly active users in 2010, and it was generating less than a billion dollars in annual revenue. Big for its time, but brands were still debating whether it was worth their attention.

Today, that same platform attracts 2.5 billion monthly active users and generates over $60 billion annually, surpassing Netflix by 33%. And it currently has a bigger grip on viewers aged 13-54 than Disney, Paramount, NBCU, FOX, Warner Bros/Discovery combined.

Last year YouTube was the number one media distributor on American television for six consecutive months, capturing 13.4% of all US TV viewing, more than any broadcaster has ever held. And we’re not talking about the laptop or the phone - these are television viewers, in their living room.

The platform that brands were tentatively experimenting with in 2010 is now the largest video business on earth, and the creative model that a handful of smart brand partnerships were quietly pioneering back then - authentic collaboration, creative trust, real partnership - is now the standard every brand is chasing.

Your skillset wasn't developed for one medium, or one company, or one industry.

It may have been built through one, but it is translatable, transportable - and urgently needed elsewhere. Even if you’re not interested in building your own YouTube channel and becoming another “Creator”, there are dozens of other new pathways to peer down. (I haven’t even mentioned TikTok or Meta or Pinterest or other media ventures whose statistics are equally astounding). So you just need a deeper understanding of the landscape, in order to translate what you already know and adapt to your new surroundings.

And in an era of hype around AI, the one thing it demonstrably cannot replace is judgment.

The taste you developed over the years is all your own. Knowing when something is working and when it isn't, holding complex creative and logistical problems while keeping everything on budget and on time, reading a room and understanding what’s needed for the moment - all of this depends on your own style, your own aesthetic, your own seasoned expertise. The machines need a human with lived experience in the driver’s seat.

Acumen from accumulated experience will continue to be more highly valued than any shiny new LLM or data pipeline right now. In fact, it is being considered one of the most valuable capabilities for mid to senior creative leaders.

The first step to finding the right work is getting clear on who you are and what you value. Assessing what you actually have. Not what your current or last job title said you had. What you’ve actually developed over the years of doing the work at a high level. The next best step is to understand the market, and the markets beyond the one you’ve been comfortable in.

The distinctions between the title and the capability or between the job and the desire - that’s the focus for The Courageous. Because if the creatives who navigate this moment understand who they are and what they want, they can recognize the right place when they find it.

In my experience, I found a way to situate myself in the right new place with the right expertise, so when I met the right people I was able to launch into all kinds of new adventures.

I might have been ahead of my time. Maybe 15 years ahead.

But your time is now. Who are you, what will you bring to the new landscape?

Drop me a line and tell me what you're working through. And tell me what came up as you read this. I read every single response.

You’ve got this.

Onward,
Kevin
Founder, THE COURAGEOUS